Monday, October 21, 2013

Stereoselective Synthesis of Vinyl Triflones and Heteroaryl Triflones through Anionic O→Cvinyl and N→Cvinyl Trifluoromethanesulfonyl Migration Reactions

by Xiu-Hua Xu, Misaki Taniguchi, Xin Wang, Etsuko Tokunaga, Tomohiro Ozawa, Hideki Masuda, Norio Shibata*

Thumbnail image of graphical abstract

Six transformations, one pot: Various di- and trisubstituted vinyl triflones, as well as several heteroaryl triflones, were stereoselectively synthesized from easily accessible gem-dibromovinyl substrates (see scheme, Boc=tert-butoxycarbonyl). The highlights of this synthetic method lie in the remote O→Cvinyl or N→Cvinyl triflyl migrations and the one-pot, three-step protocol.

Angewandte Chemie International Edition

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